Vincent B. Orange doesn’t just hang a campaign poster — he unveils it. He mounts each one with two kinds of staple gun, setting the height just so, doubling them for strength. Some he secures off-center in a technique he calls “the wave,” allowing it to flap in a breeze and thrusting it a little deeper into the consciousness of a city that has seen lots (and lots) of Orange signs in the past 24 years.

“We do kind of pride ourselves on our posters,” he said last week, standing on tiptoe to mount another one about seven feet up a light pole on Blagden Avenue in Northwest Washington.

This year the posters read “Orange for Mayor,” just as they did in the 2006 primary in which he finished with less than 3 percent of the vote. Others have said Orange for Chairman (losses in 1990 and 2010), Orange for Ward 5 (loss in ’94, wins in ’98 and 2002) Orange At Large (a win in 2011 in a crowded special election and again in 2012.) There was the Orange for Democratic Committeeman in 2008. Squeezed between the “We Buy Houses” and “Earn Extra Income” placards, thousands of “Orange for X” posters have given the perennial candidate one of the most recognized names in the city.

But for many, Orange’s latest race — his second run for mayor, his 10th race overall and his fifth citywide campaign in seven years — smacks of political profligacy.

“You never met an election you didn’t like. You run for everything,” is how political commentator Mark Plotkin challenged Orange at a Ward 3 candidates forum earlier this month. “It diminishes your stature.”

Orange rejected the jab, saying, “I lost in 2006 and the citizens of the District of Columbia brought me back. The bottom line is, I’m here because the people want me here.”

Three months into his latest effort, Orange, who has degrees in business and law, is running against a headwind of skepticism. Other than Mayor Vincent C. Gray (D), Orange is the only one in the race to have won citywide. He touts achievements as a council member that include a role in bringing Home Depot to Rhode Island Avenue NE and scraping together funds to restore McKinley Technical High School.

But critics dismiss him as an ethically challenged also-ran, saying he lacks a citywide base and has been too fierce an advocate for business owners who are also donors. He eschews the relentless door-knocking that fuels an insurgent campaign, preferring to rely on candidate forums and the poster blitz. (And a taste for the grand. Most of his opponents announced their candidacies in brief sidewalk rallies, but Orange threw a black-tie gala at Gallaudet University.)

With just over a month until the primary, Orange remains a long shot. A recent Washington Post poll placed him with 9 percent support, a bit behind three other council challengers to Gray, who led with 24 percent.

The candidate, who acknowledged that he might have thought differently about running if he had known Gray was going to pursue reelection at the last minute, says he can still win. He notes that in the poll he barely trailed Muriel Bowser, who has raised just over $1 million to his $126,000, according to the most recent fundraising reports. In the sprint to the April 1 primary, he’s focused on getting his voters to the polls and predicts he will win in Wards 5, 7 and 8.

“And parts of Ward 4,” he said of Bowser’s home turf, where he was hanging posters. At 56, he’s upbeat, energetic, bouncing on his feet. He has lost 55 pounds recently, thanks to a regimen of sit-ups and jumping jacks he pulled from his college football training manual. “There’s nothing she can do to keep me from getting 40 percent here.”

But more than the handicapping and trash-talking, Orange’s greatest strength may be his (repeatedly) demonstrated capacity for shouldering a loss. He doesn’t mind running because he doesn’t mind losing.

“At the end of the day, all is well,” Orange said at the raucous council meeting last summer at which his colleagues unanimously voted against promoting him to the body’s vice chairmanship (after Orange had nominated himself for the position). “Whether I win, whether I lose, I feel good.”

Serious about school

To understand why Vincent Orange thinks he can win anything, it helps to understand where he came from. It was an unlikely rise from one of the poorest neighborhoods in Oakland, Calif., to the cloistered realms of private schools and universities that gave him a serene confidence in his own ability — to work hard, to lead, to adapt.

“I didn’t know anything about prep school,” said Orange, a onetime peanut vendor at Oakland Athletics games. “I just knew that any environment I found myself in I could find a way to excel.”

He was the ninth of 10 children, the baby boy of a single mother who cleaned Pullman train cars on the night shift. When the family lost its West Oakland house, his mother moved them to East Oakland, where they were one of only two African American families in the neighborhood. Vincent made friends easily, and many of them were serious about school.

“I wanted to be with my friends, and they were all taking [Advanced Placement] classes,” he recalled. “So I started taking AP classes, too.”

He did well enough to win a scholarship to the Fountain Valley School, a selective prep school in Colorado Springs. The stereos in the dorm rooms and BMWs in the student parking lot were an eye-opener to the freshman whose family didn’t boast any college graduates and occasionally relied on food stamps.

“When you’re a kid, you don’t know you’re poor. You think everybody is eating cornbread and tomato paste like you are,” he said. “Suddenly I’m at a place where I know I’m going to get 21 meals a week. But I also know there is going to be mandatory study hall from 7 to 10.”

The work habits took, Orange said, propelling him through accounting and communications programs at the University of the Pacific. He came east to Washington in 1980, got a job with his certified public accountant Arthur Andersen and whittled away at two more valuable credentials: a law degree from Howard University and a master’s in taxation law from Georgetown University. But the former gas pumper and janitor always kept a gig on the side.

Recently, when signing in for an editorial board meeting at The Washington Post, he looked up at the security guard behind the desk. “I used to have your job,” Orange said. The attorney/accountant worked weekends as a guard at the newspaper for 13 years until 1994.

“I didn’t tell a lot of people at Arthur Andersen that I was working at The Post, no,” he said. “But it was a good job.”

He became interested in D.C. finances — and politics — while working on audits of the District’s books in the 1980s. He took a job with the city’s Department of Finance and Revenue and, in 1990, launched an upstart bid for council chairman against veteran Ward 2 Democrat John A. Wilson.

“I went and found out he wasn’t in a PTA, he wasn’t in an [Advisory Neighborhood Commission]. He just decided he wanted to be in politics,” said Bob King, a longtime Ward 5 ANC member. “And he has been for 25 years.”

Making a splash

Orange lost that first council race, and his next. But he won the Ward 5 seat in 1998 and began to amass what King described as a “B minus” reputation among constituents. He worked to improve school textbook distribution and pushed for the city’s April Emancipation Day holiday.

Honing his flare for the grandiose, Orange began wearing orange sport coats and referring to himself in the third person. At his recent mayoral announcement bash at Gallaudet, he asked the audience to rise just before the end of his speech, ensuring an instant standing ovation as he concluded.

“He harkens to an earlier era of D.C. politicians,” said Bryan Weaver, an Adams Morgan political activist who once ran against Orange. “To some, he’s what a city leader should look like; others kind of roll their eyes.”

He was in his second term when the “Orange for Mayor” signs appeared in 2006. Orange was crushed in the race that saw Adrian M. Fenty (D) carry every precinct in the city, and he lost again in a bid for council chair four years later.

“There is just no citywide following for him,” Plotkin said.

But Orange found a way back in a crowded special election in 2011, winning an at-large seat with just under 29 percent of the vote.

He returned as a populist. The council member once known as a fierce champion of local business came out punching for the minimum-wage increase and pay-related requirements on Wal-Mart and other “big box” employers. His slogan now: “Leaving No One Behind.”

“I’m still the businessman,” Orange said. “I just believe that if Wal-Mart’s net income was $17 billion last year, they need to share the prosperity.”

His work for local firms, particularly those that have given him money, has landed Orange at the periphery of an ethical morass that hangs over city government. In 2012, he fought efforts to reduce gas station magnate Eyob “Joe” Mamo’s dominance at District pumps. In December, he pushed to reopen a parking meter contract about to be awarded to Xerox, a maneuver that would have greatly pleased a Xerox competitor who had, through various affiliates, just given his campaign $20,000.

Most famously, he showed up at Sam Wang Produce on Florida Avenue a few days before Christmas in 2012, just as city health inspectors were about to shut it down over a rat infestation. The inspectors left with the market still open, and Orange became the first D.C. politician to be admonished by the city’s new ethics board for abusing “the prestige of the office.”

Orange dismisses the ethical complaints. He took positions on the gas and parking legislation, he said, based on policy, not donations. Questions about his donations from affiliates of businessman Jeffrey Thompson, of the kind that have enmeshed Gray in a prolonged federal investigation, have been reviewed by the D.C. Office of Campaign Finance and the U.S. Attorney, he said.

“Any and everything I received, I’ve reported, and it’s been vetted and we’ve answered every question,” he said.

As for the Wang market, Orange said he was only trying to protect the jobs of employees by getting them an extra day to clean up the infractions before being shuttered. Further, he displays a letter from the Board of Ethics and Government Accountability that says because he has fulfilled the required ethics training, “your request that your record with this Office be expunged is granted.”

“Everybody knows I went through the process,” he said. “But my record is clean.”

Staff writer Aaron Davis contributed to this report.

For more election cover, visit wapo.st/dcpolitics.

Steve Hendrix came to The Post more than ten years ago from the world of magazine freelancing and has written for just about every page of the paper: Travel, Style, the Magazine, Book World, Foreign, National and, most recently, the Metro section’s Enterprise Team.

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